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Method for preparation of N-acetyl cysteine amide

a technology of n-acetyl cysteine and amide, which is applied in the field of preparation of n-acetyl cysteine amide, can solve the problems of limited therapeutic usefulness of gsh precursors, and achieve the effects of high chemical yield and high chemical and enantiomeric purity

Active Publication Date: 2017-09-19
NACUITY PHARMA INC
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  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

The method achieves NACA in yields of up to 95% and greater than 99% enantiomeric excess, overcoming previous limitations and enabling its effective use as a glutathione precursor.

Problems solved by technology

However, directly administered, these GSH precursors have limited therapeutic usefulness because of their limited bioavailability.

Method used

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  • Method for preparation of N-acetyl cysteine amide
  • Method for preparation of N-acetyl cysteine amide

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Experiments

[0028]The following procedures may be employed for the preparation of the compound of the present invention. The starting materials and reagents used in preparing these compounds are either available from commercial suppliers such as the Aldrich Chemical Company (Milwaukee, Wis.), Bachem (Torrance, Calif.), Sigma (St. Louis, Mo.), or are prepared by methods well known to a person of ordinary skill in the art, following procedures described in such references as Fieser and Fieser's Reagents for Organic Synthesis, vols. 1-17, John Wiley and Sons, New York, N.Y., 1991; Rodd's Chemistry of Carbon Compounds, vols. 1-5 and supps., Elsevier Science Publishers, 1989; Organic Reactions, vols. 1-40, John Wiley and Sons, New York, N.Y., 1991; March J.: Advanced Organic Chemistry, 4th ed., John Wiley and Sons, New York, N.Y.; and Larock: Comprehensive Organic Transformations, VCH Publishers, New York, 1989.

[0029]Preparation of N-Acetyl Cysteine Amide (NACA)

[0030]

[0031]N-Acetyl Cystei...

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Abstract

The present application discloses an efficient process for the preparation of N-acetyl-L-cysteine amide (NACA) starting with N-acetyl-L-cysteine.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is U.S. 371 National Phase Application of PCT No. PCT / US2015 / 022910, international filing date of 27 Mar. 2015, title, METHOD FOR THE PREPARATION OF N-ACETYL CYSTEINE AMIDE, and claims benefit of U.S. Provisional U.S. Ser. No. 61 / 972,133, filed on 28 Mar. 2014.STATEMENT OF FEDERALLY FUNDED RESEARCH[0002]None.BACKGROUND OF THE APPLICATION[0003]Decreased glutathione (GSH) availability in the brain is linked to several neurodegenerative diseases including Parkinson's disease. Means of restoring GSH levels include delivery of GSH precursors, e.g. N-acetyl cysteine, N-acetyl cysteine amide (NACA) or cysteine to the brain. However, directly administered, these GSH precursors have limited therapeutic usefulness because of their limited bioavailability.[0004]The preparation of N-acetyl cysteine amide (NACA) has been previously described in J. Med. Chem. 1967, 10, 1172-1176.[0005]There is a need for developing an efficient method ...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C311/29A61K31/16C07C321/00A61K31/195A61K38/04A61K31/095A61K31/198
CPCA61K31/195A61K31/095A61K31/16A61K31/198A61K38/04C07C311/29C07C321/00C07C319/12C07C323/59C07C323/60
Inventor WARNER, JOHN C.CHERUKU, SRINAVASATHOTA, SAMBAIAHLEE, JOHN W.
Owner NACUITY PHARMA INC
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